My answer to What are the typical causes of dissatisfaction of a yacht owner vs his/her boat?
Answer by Desmond Last:
As the owner and broker of Sydney Boat Sales for 12 years I would have to say ‘size matters’.
Most Yacht owners would not be content until they had a newer 34–40′. At 34′ and above you have room for family and friends and weekends away.
After that comes age and condition. Older Yachts require lots of regular maintenance and that means time and money. The older the yacht the more likelihood of something failing.
Spending all week looking forward to going sailing, only to find the exhaust manifold has rusted through and flooded the engine, can make you look with envy at your neighbours newer yacht.
If you are a Club Racer with a good crew it will be design. Your full keel yacht will be a tortoise next to the largest fin keel design and the sail wardrobe not even in the same class.
I found that once an owner had got to his newer 34′–40′ Yacht that would be about it. That last Yacht becomes part of you and the family.